Senior Software Engineer - Site Reliability

Windscribe is a leading cyber security and privacy company launched in April 2016 and now with more than 100 million users. We believe that the internet was created so that people across the globe could have access to any type of information, no matter where they are. Our mission is to transform the internet with easy-to-use yet powerful privacy and security tools that allow anyone to circumvent censorship, access geographically restricted content, and minimize their exposure to marketers, criminals, and surveillance dragnets.

Our well-received applications have appeared on Lifehacker, Techradar, and CNET. Headquartered in Toronto, Canada, Windscribe operates two products:

• Windscribe is a suite of privacy, anonymity and anti-censorship tools for the masses.
• Control D is a modern and customizable DNS service that blocks threats, unwanted content and ads — on all devices.

Onboard in minutes, and forget about it. We have infrastructure all over the world, and right now we are looking for a Senior Software Engineer to join our Engineering team. This is a software engineering role first: you will spend most of your time writing software that eliminates operational work, not doing operational work by hand. You do not need to arrive knowing our stack in depth. You will learn it here.

About the Position

• Design, write, review, test, and ship software that improves the availability, scalability, latency, and efficiency of our services. This is the majority of the job.
• Turn operational work into engineering work: every repeated task, checklist, or validation becomes automation. A runbook is a stopgap, not a deliverable.
• Define SLOs with stakeholders and build the monitoring and alerting that enforces them — and fix or delete every alert that doesn't map to a real expectation.
• Debug production issues across the whole stack, from application code down through Linux and the network.
• Lead blameless postmortems and root cause analyses, then land the fix that eliminates the entire class of problem, not just the writeup.
• Plan capacity and cost with data; document what you build so others can operate it.
• Join our critical incident response team in an established on-call rotation. To be clear about what that means here: the rotation covers our shared infrastructure, not only the code you wrote. Learn our stack in depth — DNS at global scale, anycast networks, VPN protocols — with the team that runs it.

Qualifications & Experience

We hire for the software engineer first. Most of our stack can be learned on the job; the following cannot:

• Bachelor's degree in Software Engineering or Computer Science or similar.
• 5+ years of professional software development in one or more general-purpose languages. Go preferred; Python, Rust, and C/C++ are also great. Shell and YAML alone do not qualify.
• Automation you personally built — a tool, service, operator, distributed system, or auto-remediation system that eliminated real operational work. Expect us to ask you to walk through its design and trade-offs.
• Experience designing, analyzing, and troubleshooting distributed systems in production. Git, testing, code review, and CI as your normal workflow; comfortable in a large codebase you didn't write.
• Solid Linux fundamentals, containers, and infrastructure as code (Terraform, Ansible, or equivalents).
• Observability as a builder: you instrument your own code (Prometheus, Grafana, or equivalents), not just read dashboards.

Who This Role Is Not For

We want to respect your time, so we will be upfront:

• If your experience is primarily operating, configuring, and troubleshooting software that other people built — systems administration, NOC, or infrastructure operations under an SRE title — this role will not be a fit.
• If your observability and reliability experience is primarily advisory — SLO frameworks, dashboards, and monitoring strategy, without software you built to act on those signals — this role will not be a fit either.

Bonus If You Have

None of these are required. You will learn them here:

• Deep DNS knowledge (BIND / PowerDNS / Unbound, record types, resolution paths, DNSSEC)
• Routing experience: unicast, anycast, BGP Linux networking depth: iptables / nftables, eBPF, performance tuning VPN protocols (OpenVPN / WireGuard / IKEv2)
• Experience with bare metal fleets, hypervisors, or networking hardware (JunOS / VyOS)
• High-availability databases (MySQL, Postgres, Redis) and load balancers (HAProxy, nginx)

Compensation:

180K - 220K CAD

Stock options

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